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Chemoselective oxidative hydrolysis of EWG protected α-arylamino vinyl bromides to α-arylamino-α′-bromoacetones
- Source :
- Tetrahedron Letters. 54:4369-4372
- Publication Year :
- 2013
- Publisher :
- Elsevier BV, 2013.
-
Abstract
- Vinyl bromides bearing an arylamino group in the vicinal position are chemoselectively transformed into interesting α-arylamino-α′-bromoacetones through a straightforward oxidative hydrolysis promoted by calcium hypobromite under mild acidic conditions. Significantly, this particular combination [vinyl bromides and Ca(BrO)2] avoids bromination at both the aromatic ring and activated positions in groups substituting the amine nitrogen. The usefulness of this class of brominated ketones has been shown in a Wittig homologation.
Details
- ISSN :
- 00404039
- Volume :
- 54
- Database :
- OpenAIRE
- Journal :
- Tetrahedron Letters
- Accession number :
- edsair.doi.dedup.....102f06bb98841e245d6f000d8f22c0d7